Sodium Cyanide → Methyl 5-cyano-2-(4-fluorophenoxy)nicotinate

HRID 1293201노트

반응식

HRID 1293201 반응식
Br[C:2]1[CH:3]=[N:4][C:5]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[C-:20]#[N:21].[Na+]>C(#N)CC.[Cu](I)I>[C:20]([C:2]1[CH:3]=[N:4][C:5]([O:12][C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8])#[N:21]

참가 물질

5

반응물 2

HCID 8929Sodium CyanideHCID 57572305HCID 57572305, 화합물

생성물 1

HCID 69051385Methyl 5-cyano-2-(4-fluorophenoxy)nicotinate수율 71.3%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 7854Propionitrile용매

실험 절차

A mixture of methyl 5-bromo-2-(4-fluorophenoxy)nicotinate (step 1, 163 mg, 0.50 mmol), sodium cyanide (49 mg, 1.0 mmol), tetrakis(triphenylphohphine) palladium(0) (29 mg, 0.025 mmol), and copper iodide (9.5 mg, 0.05 mmol) in propionitrile (4.0 mL) was heated under reflux for 4.5 h with stirring. The reaction mixture was filtered through a pad of Celite®. The filtrate was partitioned between water (10 mL) and dichloromethane (30 mL). The organic phase was separated, dried (sodium sulfate), and concentrated. The residue was purified by TLC plate developing with hexane/ethyl acetate (3/1) to afford 97 mg (71%) of the title compound: 1H-NMR (CDCl3) δ 8.5 (2H, m), 7.14 (2H, d, J=1.2 Hz), 7.12 (2H, s), 3.99 (3H, s); MS (ESI) m/z 272 (M+).

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 4.5 h
  3. filtrationThe reaction mixture was filtered through a pad of Celite®
  4. customThe filtrate was partitioned between water (10 mL) and dichloromethane (30 mL)
  5. customThe organic phase was separated
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated
  8. customThe residue was purified by TLC plate

출처 및 근거

ORD 기록
ord-78234e9beb5d4c90a635478c61814a85
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238714B2

반응 노트

불러오는 중…